Water → Ethyl 6-(4-acetylamino-2,6-dichlorophenoxy)hexanoate

HRID 1634249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1634249
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:18][C:19]1[CH:20]=[C:21]([NH:27][C:28](=[O:30])[CH3:29])[CH:22]=[C:23]([Cl:26])[C:24]=1[OH:25].O>CC(C)=O>[C:28]([NH:27][C:21]1[CH:22]=[C:23]([Cl:26])[C:24]([O:25][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:19]([Cl:18])[CH:20]=1)(=[O:30])[CH3:29]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 117544Ethyl 6-bromohexanoateHCID 100821803',5'-Dichloro-4'-hydroxyacetanilide

Produkt 1

HCID 18677764Ethyl 6-(4-acetylamino-2,6-dichlorophenoxy)hexanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

13.3 ml (74.9mmol) of ethyl 6-bromohexanoate and 52.1 g (160 mmol) of cesium carbonate were added to a solution of 15.0 g (68.1 mmol) of N-(3,5-dichloro-4-hydroxyphenyl)acetamide in 300 ml of acetone. The suspension was boiled under reflux for 8 hours, and then 600 ml of water were added. The mixture was extracted twice with 400 ml of dichloromethane and with 400 ml of MTB ether each time. The combined organic phases were washed with water and concentrated in a rotary evaporator. The product was employed in the next step without purification. Crude yield was 30 g.

Aufarbeitung

  1. temperatureunder reflux for 8 hours
  2. extractionThe mixture was extracted twice with 400 ml of dichloromethane and with 400 ml of MTB ether each time
  3. washThe combined organic phases were washed with water
  4. concentrationconcentrated in a rotary evaporator
  5. customThe product was employed in the next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-1f704998465f455ebffc5809c9a41686
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06506778B2

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